An Efficient Synthesis of 2,4-Disubstituted Quinolines by Electrophile-Mediated Cyclization Reactions of 2-Isocyanostyrene Derivatives
作者： Kazuhiro Kobayashi , Kenichi Takagoshi , Shizuka Kondo , Osamu Morikawa , Hisatoshi Konishi
DOI: 10.1246/BCSJ.77.553
关键词:
摘要: A novel quinoline synthesis starting with 2-isocyanostyrene derivatives is described. The treatment of aldehydes (or acetone) in the presence a catalytic amount diethyl ether-borontrifluoride afforded carrying 1-hydroxyalkyl substituent at 2-position. use acetaldehyde acetal or phenyloxirane as an electrophile under same conditions gave corresponding derivatives, 1-ethoxyethyl 2-hydroxy-2-phenylethyl 2-position, respectively. 2-Isocyanostyrene reacted N,N-dimethyliminium salts without any catalyst to give 2-(1-dimethylaminoalkyl)quinolines.
csj.jp参考文章(55)
CH McAteer, M Balasubramanian, R Murugan, None, Pyridines and their Benzo Derivatives: Applications Comprehensive Heterocyclic Chemistry III. ,vol. 7, pp. 309- 336 ,(2008) , 10.1016/B978-008044992-0.00606-4
T. Suresh, R. Nandha kumar, P. S. Mohan, A Facile approach to dibenzo [bf| [1,6] naphthyridines using Vilsmeier Conditions Heterocyclic Communications. ,vol. 9, pp. 83- 88 ,(2003) , 10.1515/HC.2003.9.1.83
Daniel Dubé, Marc Blouin, Christine Brideau, Chi-Chung Chan, Sylvie Desmarais, Diane Ethier, Jean-Pierre Falgueyret, Richard W. Friesen, Mario Girard, Yves Girard, Jocelyne Guay, Denis Riendeau, Philip Tagari, Robert N. Young, Quinolines as potent 5-lipoxygenase inhibitors: synthesis and biological profile of L-746,530. Bioorganic & Medicinal Chemistry Letters. ,vol. 8, pp. 1255- 1260 ,(1998) , 10.1016/S0960-894X(98)00201-7
Fatima Zouhiri, Jean-François Mouscadet, Khalid Mekouar, Didier Desmaële, Delphine Savouré, Hervé Leh, Frédéric Subra, Marc Le Bret, Christian Auclair, Jean d'Angelo, Structure-activity relationships and binding mode of styrylquinolines as potent inhibitors of HIV-1 integrase and replication of HIV-1 in cell culture. Journal of Medicinal Chemistry. ,vol. 43, pp. 1533- 1540 ,(2000) , 10.1021/JM990467O
J. Gantier, A. Fournet, M. Munos, R. Hocquemiller, The effect of some 2-substituted quinolines isolated from Galipea longiflora on Plasmodium vinckei petteri infected mice. Planta Medica. ,vol. 62, pp. 285- 286 ,(1996) , 10.1055/S-2006-957883
Brindaban C Ranu, Alakananda Hajra, Suvendu S Dey, Umasish Jana, Efficient microwave-assisted synthesis of quinolines and dihydroquinolines under solvent-free conditions Tetrahedron. ,vol. 59, pp. 813- 819 ,(2003) , 10.1016/S0040-4020(02)01587-9
Richard Smith, Tom Livinghouse, Alkaloid synthesis via the intramolecular imidate methylide 1,3-dipolar cycloaddition reaction Tetrahedron. ,vol. 41, pp. 3559- 3568 ,(1985) , 10.1016/S0040-4020(01)96709-2
Lisa M. Nogle, William H. Gerwick, Diverse Secondary Metabolites from a Puerto Rican Collection ofLyngbyamajuscula Journal of Natural Products. ,vol. 66, pp. 217- 220 ,(2003) , 10.1021/NP020332C
Alain Fournet, Renaud Mahieux, Mohammed A Fakhfakh, Xavier Franck, Reynald Hocquemiller, Bruno Figadère, Substituted quinolines induce inhibition of proliferation of HTLV-1 infected cells. Bioorganic & Medicinal Chemistry Letters. ,vol. 13, pp. 891- 894 ,(2003) , 10.1016/S0960-894X(02)01085-5
Hector Nakayama, Maria Elena Ferreira, Antonieta Rojas de Arias, Ninfa Vera de Bilbao, Susana Torres, Alicia Schinini, Alain Fournet, Experimental treatment of chronic Trypanosoma cruzi infection in mice with 2-n-propylquinoline. Phytotherapy Research. ,vol. 15, pp. 630- 632 ,(2001) , 10.1002/PTR.877